Strategy Questions

It’s possible that your CTO is focused on a very specific piece of the puzzle. Perhaps they are focused on the applications that your company develops and sells. They manage the development team and the technology that the applications live on. In this case, the CIO (strategic) role is missing. Hiring a strategic managed IT service is one great way to outsource to CIO role without adding to your overhead costs. 

Regardless of the industry you are in, having a strategic plan on how to use technology is crucial to your company. A flower shop still needs to make sure that inventory is updated, and that an efficient payment processing method exists. On the surface, the flower appears to function the same as always, but the technology is very different and that leads to very different results. When your business is more complex or operates on a larger scale, the principles behind the technology strategy still remain the same. 

As your virtual CIO, Now IT Works offer business road maps. However, you’ll still need to decide where your business is going. It’s our primary role to keep your technology running and then we look at ways to make you more efficient. We’ll ask questions to get a baseline for your business. Then, we guide or offer suggestions quarterly, yearly, or when you ask. 

All decision makers receive a copy of the strategic plan. It typically consists of 3 major parts–a list of projects, a timeline for completion, and the budget. In addition, you’ll want to decide who needs to be involved and how changes will be communicated to the rest of the team. The goal is to keep everyone on the same page. 

This matters most since you’ve invested your resources in the project. It’s about defining each piece of the project clearly and on a micro level. Then we track progress by assigning a “score” to each project. In addition, you’ll begin to realize benefits from greater efficiency. Sales convert more quickly, operations run more smoothly, and AR comes in faster. 

Of course. Now IT Works believes in small businesses like yours. What should you do? Just begin. Gather your leadership and your IT person (in-house or outsourced) and begin to develop the plan. You’ll be better off for it, even if you decide to hire a managed IT firm in the future. 

You will need to make changes. We advise meeting each quarter to determine what changes need to be implemented. We act as your IT guide or top advisor.

Now IT Works believes in communication. First, you can let your team know about your intentions once you have made a decision to move in a particular direction. Once things are implemented, you can communicate more specifics to avoid any confusion. 

Hiring an outside managed service provider helps to smooth out technology relationships withing your company. Your team now has someone you can trust to provide solid advice so you can make the best decisions. 

Have you heard this proverb before? The best time to plant a tree was 20 years ago. The second-best time is now. Your competition likely has an IT strategy plan. We always tell small businesses today that every business is an IT business. So, really this is an integral part of your business plan. Now IT Works keeps things focused on your business needs so you’ll never feel resources are being wasted. 

Security Questions

Yes, you’ll want an antivirus software that offers web and internet protection. Though Windows 11 comes with built-in antivirus software, it might not be able to protect your web browsing activity or malicious links. 

It will take an analysis of your company to see where the security holes exist. However, we always recommend multi-factor authentication. You’ll also want an email security suite, regular firewall updates, a password policy, user review, and an IT security assessment.

You’ve got options. 1. Give them their own password management tool and show them how to use it. 2. Or implement a company-wide password management tool or single sign on to grant access to specific individuals for specific sites. 

A password manager stores all of your passwords in a single location. It will also automatically input the password when you log onto a saved site. 

An identity manager tool allows you to group your websites together (Office 365, Salesforce, Quickbooks, Slack, etc.) by using a single username and password. This works with single password policies and each will update when the master is updated. 

A disaster recovery plan includes evaluating all backups and ensuring any redundant equipment critical to recovery is up-to-date and functioning properly. This document is a subsection of the Business Continuity Plan. 

BCP consists of your business’s impact analysis, risk assessment, and overall business continuity strategy. 

So, if your server goes down, you’d look to the DRP to understand how to get systems back online. 

However, if the building you’re in burns down, you’d need the DRP but you’d also need a BCP to understand how you’d continue to conduct business under these circumstances.  

Productivity Questions

That can happen, especially now that we purchase more software programs and SAAS (software as a service or subscriptions). Many of times, we have crossover, or more than one piece of software that provides the same function. We always recommend analyzing new software before purchase and understanding why you are buying it. Consider implementing a process that holds the team accountable before adding anything new. Many times, we work with clients to make the most out of their current software. If you’re only using a software to 70% capacity, then you’re not getting the most out of it. We find ways to be creative and make changes when necessary. 

  1. Set the right company culture for your employee. establish expectations, communicate, and offer positive feedback. 
  2. Onboard your employees the right way when it comes to technology. Make sure they have the tools to help them do their job more efficiently. Do we need to set up special email rules? Do they need special software or access to something existing? 

Mostly, this is driven by the process you desire for your business. 

Do you archive emails? Is this part of compliance or proactive leadership? If you archive, how long? Have the discussion around compliance and what makes sense. 

Sometimes we have balance security and convenience or productivity. If you have a super secure email policy, then this can hinder communication. This is another conversation.

In addition, you’ll want to decide about automation. For example, if the email has a certain format, you might automatically send it securely. 


This is tougher to answer in a forum. However, there are 2 main points. 

  1. Set the right culture and establish your expectations. 
  2. Hire the right talent, but also plan to have an onboarding process. Set up times to check in and have accountability for your team and the employee.